When I first re-entered the dating world a little over 2 years ago, it was a rollercoaster of emotions–I’d have the highs of making a new connections and thinking it could be the perfect person, the anxiety of not knowing the “right” thing to say on a message or on a date, and then the lows of being ghosted or let down by a date not meeting my expectations.  

Since then, I’ve learned a lot about what it takes for me to have a healthy dating life that’s helped me look at dating not with dread or with exhaustion and feeling constantly disappointed or let down–but with the excitement of a new adventure in meeting new people. 

After all, I learned that dating isn’t about finding the right person. It’s about me becoming the person that I’d want to date. 

My relationship with myself is the most important thing I can do to have a healthy relationship with someone else. 

I’ll explain more in the lessons that follow. As a life coach, I’ve also been able to see these lessons help my clients in their dating lives, for men, women, straight and queer people alike. So if you’re here, I’m sure you’ll find something that you relate to and that can help.

After all, dating doesn’t need to be so hard, and I’ll show you how. But first, a little context about my story: 

My late entry into the dating world

I was in a relationship from when I was 19 until 27, at which point I’d never been on a dating app before. I’d also not had much time under my belt being openly gay and single (it was only weeks between when I came out and when I found my partner that I’d be in a 7.5 year relationship with). 

So the dating world was new upon newness, and it was really overwhelming. 

The thing that I think played such a big role for me in having a healthy dating life was that after my breakup, I’d waited about a year before I started dating again. I spent my time working on my own self-worth and self-esteem, and healing from the baggage I had so I didn’t bring that into a new relationship. (By the way, spending time alone to get this stuff sorted out is something I highly recommend. I found that if you can’t be happy single, you won’t be able to be truly happy in a relationship, either.)

Now, after I’d done that work, I entered the dating world (especially online dating) and realized, “Oh, I have to market myself?” Ugh. It felt gross and unnatural. “I’m supposed to ‘convince’ people to want to swipe on me?” Ew. 

Needless to say, I made a lot of mistakes and missteps along the way. I had a lot of unrealistic expectations about what dating was all about. And after going through that, I thought I’d share the lessons I’ve learned from being in the dating world so you can hopefully avoid some of the mistakes that I’ve made.

1. Dating isn’t about finding the right person

I know this probably sounds counterintuitive. “What do you mean? Dating is all about finding the person you want to be in a relationship with,” you might be thinking.

Here’s another take: Dating is about meeting new people, and in the process, learning and discovering who you really are. 

It’s about finding out what you like in a potential partner, and what you don’t like. It’s about learning about what you enjoy spending time doing and what you can’t stand doing. It’s about discovering what’s comfortable and what are things you dread. What are the things you’re nervous or shy about?

Dating is all about finding yourself and who you are, what you really want in a partner– and once you do that, the right partner becomes a lot easier to find (or easier for them to find you).

2. It’s about learning who you want to become 

I kept noticing that I was attracted to people on dating apps with cool travel and outdoor pictures. People with hobbies and unique interests seemed really interesting to me. 

In my mind I said, “Wow, I hope I can get a date with that person so we can go skydiving together, or so they can teach me to play drums, or so they can take me surfing, etc.” 

It was then that I had a huge realization: Wait, I don’t need a date or a partner to do those things.

And then, I started doing those things myself, and having so much fun in the process (check out my Instagram for fun skydiving and drum videos). Funny enough, those pics then became the experiences I’m most proud to share about myself on my profile as well. 

3. The goal of a date is not to get them to like you!

The key is not feeling like it’s your job to impress anyone: it’s to discover if there’s a connection you’d like to pursue.

This is again where it was critical to have a healthy relationship with myself before I started dating. Otherwise, I’m looking for that external approval and am just going to act motivated by wanting them to like me.

When I’ve done the work on myself that I don’t need them to like me, it’s so much more fun, and freeing! 

4. How to not ghost people

This was a lesson I wasn’t expecting. The majority of the dates I went on, I was the one not interested in pursuing any further. I then had to learn how to let someone go with dignity, without just ghosting them (which on the surface, seems like a much easier solution because it avoids the brief discomfort of being honest). 

I’ve had to learn how to say, “Hey, I had a really great time meeting and learning about you. This isn’t quite the vibe that I’m looking for in a relationship, and I wish you the best of luck with everything.”

It actually saves me a lot of tension and anxiety as well. Just about everyone I’ve said this to has taken it well. I’ve had a few people react poorly (which shows more about their character, and validates my decision to not pursue anything further), but it’s definitely the minority. 

And coming from someone who has been ghosted myself, clear communication is gold, which leads to my next point…

5. Communication and self-awareness is key– and sexy

It’s a shame that the most important things in human relationships, in my opinion, are things  we’re often not taught about them in any structured way. It’s up to us to pursue learning more about developing skills in communication and self-awareness, and most people don’t put in the work if they’re not prompted.

For me, gauging someone’s communication and level of self-awareness makes it easier to filter out who I’m not going to enjoy spending time with–if there aren’t healthy communication and listening skills, and if there’s not a good deal of self-awareness, I’m not interested.

I’ve also found that those are qualities that frankly are the biggest turn ons for me.

One of my former partners used to say, “Hey, I need some time alone so I can do some journaling,” and I would instantly want to kiss her because of how sexy that was for someone to communicate so clearly and also take ownership over knowing what they need in order to take care of themselves. (No joke–it was one time when we were both doing some journaling on our own sitting near each other that I first said, “I love you.”)

And this can only happen if you know what you really want and don’t want, which brings me to…

6. Be clear about your deal breakers and must-haves

Dating helped me realize my deal breakers and my must-haves that I didn’t realize before. For instance, for me, when I see someone who looks super attractive, and then their profile says how they can’t wait to find someone to smoke and party with, I already know that’s not going to be a good fit, no matter how well the other parts of the relationship may be.

Don’t like dogs? It’s a no, I pick Luca over you anyday (and also, what’s wrong with you?).

Are you married? Yea, not going to work for me.

Are you unkind? Byeeeeee.

Getting clear about what those things are also helps me not waste my or anyone else’s time by connecting with folks that I know will not be a good fit. It’s so relieving to not feel like I need to change or convince anyone of anything. Speaking of convincing…

7. You don’t need to convince someone to like or want to go out with you

This has been big for me–not needing to control the outcome and learning to trust that if someone really is interested in me, they’ll find a way to make it work so we can get together. 

Sure, sometimes things actually are hectic. Sometimes things do come up. But when we have a date scheduled, and then there’s randomly something that comes up at the last minute (like a fridge being delivered? I really got that from someone one time) and then I never hear from you again, that’s a sign of someone with poor communication skills. 

How much more effective and mature would it be to say, “You know, it’s been great chatting, and I don’t want to waste your time or mine, so I don’t think I’d want to pursue this any further right now. I wish you the best.”

I’d say, “Sounds great, thanks for letting me know! You too!”

And it makes me have so much more respect for that person as well. 

See? Good communication is like magic. Which means I need to be okay with the outcome, even if it’s….

8. Getting comfortable with rejection

I know, no one likes this. It’s people’s greatest primal fear. But the cool thing is, get this: 

Once you’ve really reached a point of accepting yourself, you won’t worry as much about other people rejecting you. 

Will it still be a bummer? Sure. But it won't be so paralyzing that it prevents you from taking action. And it won’t have you crawling up in bed for weeks afterwards just trying to recover.

As Tyler Henry says, “You may be the juiciest peach, but you’re gonna find some people just don't like peaches, and that’s okay.”

You’re a juicy peach, love! Don’t waste your time on people who don’t like peaches! 

The woman who rejected me in London (because we all love those stories)

Recently I went on a 2-week backpacking trip in Europe. In London one night, I went out for dinner at a fancy restaurant at a fancy hotel (which I was staying in because everywhere else was sold out and I didn’t make plans far enough in advance). 

At first, I just popped in to look at the menu, but the hostess lady there absolutely captivated me. She was so beautiful, and her energy was so attractive. And when she asked if I wanted a table, my heart was beating so fast and I couldn’t say no. 

Then, I was even lucky enough to have her as my waitress. I was nervous like a little school girl. I asked her what was good on the menu and when she said the roasted beets, the only thing I could verbalize without stuttering too much from nervousness was “I’ll take that!” (disclaimer– I’m not normally this person at all. I’m rarely that nervous around people, but a woman I’m really attracted to?-OMG, death by butterfly attack.) 

Long story short, at the end of the dinner, I complimented her and asked her out. She said no and that she had a boyfriend. 

I was definitely bummed, but you know what would've been an even bigger let down and disappointment for me?

It would’ve been if I left my Europe trip telling all my friends about the beautiful lady I met in London, and never even put myself out there to see if there was an opportunity for a date.

I’d much rather get rejected than always wonder, “What if…”

I had a blast the rest of my Europe trip, and it was a fun story I knew I’d bring back to my friends. A healthy relationship with myself is what allows that to happen. And that’s possible for you, too. Speaking of going for it…

9. No one likes making the first move

Wow. I didn’t expect this. I mean, I knew it was true, but I didn't realize to what extent it was true across the board– men, women, and everyone in between. 

It feels like being at the middle school dance where everyone is sitting down on the perimeter of the room and the whole dance floor is empty because no one has the courage to start dancing. 

It’s really not a big deal. I don’t overthink things. If I find someone attractive, I let them know about it, and I ask them out in a kind, genuine way (I have no advice on pick up lines). 

I don’t know if it’s because I’m queer or just because I’m confident enough in myself, but I find myself often making the first move and reaching out. The key here is to not hang all your self-worth on getting a response back. Reach out because you genuinely want to say something to that person, and accept that the results are out of your hands.

10. Playing games and overthinking is overrated

I really can’t believe all these games and stupid rules about when you can text back are still a thing. Can we just stop and be adults? 

If I like you, I’ll tell you. In clear English. Not in ancient hieroglyphics that’ll take you and your team of researcher friends weeks to decipher.

Again, clear communication is sexy! Why don’t we do that more? (Although, I think it’s not that most people are playing games, it’s that they’re poor communicators and really are doing the best they can because they don’t have the skills). 

After a date, I don’t look at the clock and wait 18 ½ hours before sending a specific “32-character long text with specific emojis present and others not present because they give the wrong vibe.” This isn’t a science experiment. It’s a conversation between two dynamic human beings.

Just be real. Stop overthinking. If you like someone, say it. If you can’t wait to go out with them again, say it. If you don’t actually want to grab sushi on the date, say it. If you’re still hungry after lunch together and want to order dessert, order it (speaking from experience). 

Speaking of amazing desserts…

11. Have dates doing things you’d want to be doing anyway. 

This was key for me! First off, I’m not looking to grab dinner and have a whole evening spent with someone who I just met if I'm not sure that we’ll even click. I prefer smaller time-commitment dates like coffee (which can be anything from an hour to much longer if it’s going really well).

One thing I’ll also do is invite people on a date doing things I already wanted to do or try (this is also the perk of making the first move and asking them out– you get to propose the spot to go or thing to do!). 

Whether it’s that one new coffee shop I’ve been meaning to go to, that art gallery, the festival downtown, the farmers market (talk about an interesting date– seeing how they appreciate good food!), or a show, a bike ride, or a hike–why not spend your date doing things you would actually want to do? 

That way, even if the date itself is bad, I’m doing something I genuinely wanted to do anyway. And it’s also a way to gauge if you have some similar interests.

12. Quality over quantity of dates

At one point, I was all about just getting as many dates as I could. That got boring, QUICK, when I realized 3 minutes into a date that I was totally not interested in any sort of connection with this person, and couldn't wait for the coffee date to be over (I’ve heard of some people leaving within 10 minutes, but I’ve never actually done that).

That being said, the quality of the date is much much more important than quantity. So these days, I’d rather have one date that actually holds potential for an interesting conversation than a bunch of dates that I’m cringing the whole way through.

But again, this all comes back to having a healthy relationship with yourself, first (noticing the common theme?). Otherwise, you might look to go on dates as an ego boost or as a distraction from the work that’s really important in getting to know yourself, first.

13. Some people just want to chat–not actually date

Some people just want to chat or talk, but never actually meet up. It took me some time to realize this. For me, I typically don’t need to chat very long to realize whether this is someone I’d like to meet in real life or not. So it’s typically just within a day or a few days before I ask if someone wants to meet in person. 

And if it’s a no, I just pack it up and keep moving. Again, self-worth, I don’t need to convince anyone to want to spend time with me.

So it’s worth getting to know early on– are you both on the same page about wanting to actually meet in real life, or are they looking for a pen pal? 

14. If it seems perfect, but it isn’t working, it’s probably not perfect.

The thing with dating is that you start to create a story in your mind of who this person is based on the tidbits of information that you have. And many times, we fill in the blanks wrong. 

Many times, I’ve told myself a story about how this person was PERFECT for me, only to struggle with actually getting the conversation to move along or a date scheduled.

That means it wasn’t actually perfect after all! It’s not about anything you did wrong. Let it go, sista. They ain’t meant for you.

15. Be open to being surprised 

One time I went on a date with a woman who lived in another state than me, 4 hours away. We had such a great chemistry just talking, that we both decided that we really wanted to meet up in person, even though it seemed really impractical. 

Now, I normally wouldn’t want to consciously date someone who lived so far away, but I didn’t project, and just went with how the connection was developing, and it felt natural to meet up, even if it would take a two-hour drive for each of us to meet up half-way. It didn’t end up working out, but it’s still a connection I learned a lot from, and it taught me a lot about myself (I wrote this piece based on that experience: How to Know If You Click with Someone (Gravity)). 

So what I realized is—be open minded, you might be surprised. (And by that, I mean open minded within the boundaries of your deal breakers. Not in a way that violates your values in a partner/relationship.) 

16. Learn how to flirt via text

Okay I’m a little embarrassed by this one, but it’s true: I really had no idea how to flirt or show interest in someone via text before I started online dating. I’d been in one relationship for the majority of my 20s, so this was all new for me. 

At first I’d try to be someone else, thinking it meant sending a message that should be read with a whisper in a super seductive voice– that’s who I thought I needed to be to be flirty.

It felt so unnatural for me. 

Over time, I realized that it wasn’t just an unnatural feeling because it was new, it was unnatural because it wasn't authentically being me. I much prefer to flirt with clear communication and my sense of humor, because that’s what I find attractive coming from others.

Example: “Your video of you playing drums is super cute. I love that you look like you’re really having fun zoning out in your own little world.” (Oh really? You’re so sweet to say that about my drumming, I’m flattered.)

In other words, I’ve had to find my authentic way of communicating how I feel, and communicating that I’m interested in someone. It takes some time, but eventually, it’ll start to feel more natural.

17. Each date can teach you something–even bad dates 

I've had some trainwreck dates. I once had a date with an outwardly racist guy who wasn’t the biggest fan of queer people (HARD PASS). I’ve had a date with a woman from whom I thanked the heavens that it started raining during our date so I could leave earlier than expected (I remember leaving the date literally running to my car–I blamed the rain for moving so quickly).

But I learned something valuable from each of those encounters about what I want, what’s important to me, and what I don’t want.

It takes a bunch of bad dates to even recognize what a good date really is. (Mic drop.)

18. Don’t be boring–have authentic conversations

I can’t tell you how many times I’ve heard from dates and potential dates, “This is the most interesting conversation I’ve had with anyone on this app, or on a date.” (And believe me, that wasn’t any earth-shattering conversation, it was just having a normal, real conversation showing interest in the other person and being myself.)

It’s a compliment and flattering for sure, but it’s also really sad that more people aren’t having real, authentic conversations, or feeling like they need to put on an act. How boring it would be to have the same date routine over and over again like groundhog day just with different people.

I’d get so bored of talking about the same thing over and over. So I’m just real and talk about whatever is specifically coming up that day or that I’m interested in about that specific person. 

Each date I’ve been on and each conversation I’ve had has been entirely different–and I wouldn't have it any other way.

Some people can have multiple conversations at once, others can’t.

On a side note: since my conversations are all fairly deep and unique, I’m not having the same conversation with multiple people at the same time. That normally means I can’t really focus well on juggling multiple conversations at the same time with people I’m interested in. That’s just me, I'm not that great at it. 

So again, when I’ve been in the process of figuring out a time to schedule a date or something with someone, I’ve needed to communicate with any other people I may have matched with and say, “Hey, I’m not available to chat more for the next few days at least because I have some other things I’m focused on that are pulling my attention. Maybe we can reconnect at another point?”

And if you’re talking to someone who values good communication skills, you’re instantly higher up in their view of you.

19. Learn the feeling of “attraction” versus “nice person to hang out with”

It took me a while to understand what the feeling of attraction really is. Especially for a queer person like me, I was taught my whole life that “attraction” is what I naturally felt towards guys (because society assumed I was heterosexual). But what I always felt towards guys was something friendly, like a brotherly vibe of let's hang out and climb trees and do stuff!

It’s taken me time to realize what attraction really feels like, even with women! I’m someone for whom it’s easy to have conversations and connect with people, which makes it even more difficult to realize, when do I really like someone?

I realize that for me, there’s an unmistakable feeling in my stomach when I’m with a woman I’m attracted to. There’s a nervousness and butterflies and a lot of blushing on my part. My heart beats really fast. And I can’t wait to talk to her again. 

That’s very different from, “Oh, this was cool to hang out.”

But it takes some time and getting to know yourself to be able to identify what the clues are for you, specifically.

20. The only question I need to ask myself after the date: do I want another one?

I don’t need to know whether this is “the person” and what all the logistics will look like and if they’ll work out for us to build a life together and yada yada (see how exhausting that all sounds already?).

Instead, after a date, I ask myself one question, “Am I excited at the idea of having another date with this person?” 

If the answer is “Sure,” - that’s not good enough. 

I’m looking for a pull, a “Yes, absolutely! We really hit it off.”

21. Sure, photos aren’t everything, but they do say a lot

Yes, I agree that we shouldn’t judge a book by its cover. However, there is something to be said for the type of pictures someone chooses to put on their profile. 

Bathroom selfies in bathing suits? Okay, I’m doubting you want a serious relationship. 

Filters on every single picture? Not quite my vibe.

It also forced me to look at my own profile. At some points in time, I wasn’t looking for anything serious, and my pictures reflected that in a subtle way. Then, once I decided I wasn’t looking for something casual anymore, I changed my photos on my profile so I wasn’t just giving a flirty, let’s get together and have fun kind of vibe.

Again, this is about knowing what you want, and then being okay with saying no to what doesn’t line up with it.

22. It’s not worth obsessing over the apps 

Okay, I’m totally embarrassed to say this, but when I first downloaded those apps, I was straight up addicted (they’re engineered to be that way). I was obsessed. I was so convinced that the harder I worked at swiping and the more time I spent on the apps, the faster I’d find my person.

Not true. It’s an app (designed by a company to make money, by the way). It’s not a matchmaker from the heavens.

I would spend HOURS on this thing. I remember one time I was in the bathroom (don’t make fun of me) and was so caught up swiping that I sat on the toilet for hours, and the only thing that actually got me to get up was that my phone died. 

These days, I put a max on how much time I spend on those things, or I limit it to just checking it once a day. 

It’s just not worth it for me. I’d rather put my energy into building a life I love and focusing on what I do have control over. 

23. Don’t be afraid to show yourself (video, audio)

It was amazing to me how shy people are on these apps (it was also when I first started realizing that I’m more self-confident than most of the people I came across).

When I realized that sending audio or videos or Facetiming gives me more information about a person than days and days of messaging, I started defaulting towards that (time efficiency!). It’s surprising how many people would not be comfortable sharing that part of themselves. It’s like they’re hiding behind texts. 

It’s amazing how a 15-audio or video clip has so much information in it about someone's energy, their vibe, their personality. That, to me, is where authentic connections live. Not just in the 2 lines of a bio you can write about yourself. 

Why not just take a video or audio clip–you are who you are, if we go on a date I’m going to find out anyway, so why not just cut to the chase and save us both the time?

Don’t tell people about yourself, show them. 

24. Sometimes online dating does work

After breaking off my engagement from my long-term partner, I had worries about never being able to fall in love again, never finding someone, never feeling safe, etc.

I then developed a year-long relationship with someone I’d met off a dating app. It was actually the healthiest relationship I’d ever been in, and really was such a profound experience for me on so many levels. It taught me so much about myself.

(Here’s a poem I’d written about that relationship, if you’re a sappy romantic like me and love love stories: Being with You.)

Even though it ended, it was hugely impactful for me and also created a bond and friendship with that person that I’ll hold onto forever. All that we went through together, those shared times and experiences, the pivotal moments and firsts for both of us–it was really magical. And, it also reached a point where it needed to end, which is okay, too. 

And yes, it ended, which brings me to my final point…

25. Relationship success isn’t gauged on how long it lasts

I could probably write a whole article just on this last point, but for the sake of you already sticking with me for this long, I’ll keep it short. 

I’d always thought a successful relationship was one that lasted a long time, and a failed relationship is one that ended.

That couldn't be further from the truth. How many unhappy couples do you know? How many people do you know that have been married forever but they’re not actually happy with each other, they’re just settling for the complacency of the relationship because it’s too much work to make a change?

For me, an unhealthy relationship that lasts a long time isn’t success. And yet that’s exactly what I believed for the course of my 7.5 year relationship. I thought it was something to be proud of that I was someone who could commit and hold down a long-term relationship with a partner.

Yet, the dynamics of that relationship was so unhealthy, that it probably should've ended about 6 months in (I know, that’s a tough truth to swallow).

So today, the goal for me isn’t to have a “long” relationship, but a healthy one. To take the lessons and the good experiences for as long as they last, and then to be able to gracefully let it go when it’s causing more pain and isn’t working anymore. 

Dating gets a lot easier when you get to know yourself first

Listen, dating is hard enough. But if we’re doing it without a strong foundation of who we are, first, it’s unnecessarily stressful. It becomes that rollercoaster of emotions that we hear so many friends talk about.

It doesn't need to be that way. 

By focusing on yourself first, you can get a clear idea of what you’re looking for in a relationship: I don’t mean the vague “someone to share my life with”-- I mean the specifics: Paint me a picture of your ideal Tuesday together. How do you communicate? What does it look like when you disagree? What do your fights look like?

Dating gets exponentially easier when you’ve already done the work on yourself to know who you are, what you want, and what you have to offer.

Then, you’re not looking for a relationship from a place of need–you don’t need a partner to make your life happy or successful or complete.

You can create all of that yourself. Then, you can just have someone to join you for the ride, as two complete people, who don’t need each other in a cycle of codependency, but choose to be with each other because it makes their lives better.

As a life coach, I get to witness my clients have breakthroughs in their self-discovery that translates into healthy dating from a place of fully accepting who they are, and not needing validation from someone else. They also get comfortable with rejection (because it’s inevitable), which means that they don’t have as extreme highs and lows throughout navigating the dating world. 

Not sure where to start with your self-discovery journey? Schedule some time for us to chat, and let’s get you on the path to creating the life you want.